CN108440678B - A kind of preparation method of different molecular weight amylose-fatty acid complex - Google Patents
A kind of preparation method of different molecular weight amylose-fatty acid complex Download PDFInfo
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- 239000000194 fatty acid Substances 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 229920000856 Amylose Polymers 0.000 claims abstract description 48
- 239000000725 suspension Substances 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 24
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 23
- 229930195729 fatty acid Natural products 0.000 claims abstract description 23
- 239000002244 precipitate Substances 0.000 claims abstract description 9
- 238000005119 centrifugation Methods 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 9
- 238000009423 ventilation Methods 0.000 claims description 9
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 8
- 238000004108 freeze drying Methods 0.000 claims description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 8
- -1 polytetrafluoroethylene Polymers 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 239000006228 supernatant Substances 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 7
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 7
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 4
- 239000005639 Lauric acid Substances 0.000 claims description 4
- 235000021360 Myristic acid Nutrition 0.000 claims description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 4
- 229960002446 octanoic acid Drugs 0.000 claims description 4
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 abstract description 13
- 235000013305 food Nutrition 0.000 abstract description 6
- 229920002472 Starch Polymers 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 235000019698 starch Nutrition 0.000 abstract description 5
- 239000008107 starch Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- 102000004190 Enzymes Human genes 0.000 abstract description 3
- 108090000790 Enzymes Proteins 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 238000013329 compounding Methods 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000007865 diluting Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 238000007789 sealing Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003805 vibration mixing Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 238000012545 processing Methods 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920000294 Resistant starch Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000021254 resistant starch Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 125000003535 D-glucopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B33/00—Preparation of derivatives of amylose
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
本发明公开了一种不同分子量直链淀粉‑脂肪酸复合物的制备方法，属于生物可降解材料制备领域，本发明将淀粉悬浮液装入反应釜中，加入脂肪酸，混合密封后置于烘箱中加热，使直链淀粉和脂肪酸进行在反应釜中复合，得复合物后用热水稀释，离心分离收集沉淀物，洗涤后冷冻干燥，得到直链淀粉‑脂肪酸复合物。本发明通过在水中将高分子量直链淀粉和不同碳链长度的脂肪酸复合，制备不同分子量的直链淀粉‑脂肪酸复合物，无需使用有机溶剂、酶或酸碱，绿色环保，有利于直链淀粉‑脂肪酸复合物在淀粉食品和非食品工业中的应用。The invention discloses a preparation method of amylose-fatty acid complexes with different molecular weights, which belongs to the field of biodegradable material preparation. In the invention, starch suspension is put into a reaction kettle, fatty acid is added, mixed and sealed, and then placed in an oven for heating , the amylose and fatty acid are compounded in the reactor, the compound is diluted with hot water, the precipitate is collected by centrifugation, washed and then freeze-dried to obtain the amylose-fatty acid compound. The present invention prepares amylose-fatty acid complexes of different molecular weights by compounding high-molecular-weight amylose and fatty acids of different carbon chain lengths in water, without using organic solvents, enzymes or acid-base, green and environmental protection, and is beneficial to amylose ‑Application of fatty acid complexes in starch food and non-food industries.
Description
Technical Field
The invention belongs to the field of preparation of biodegradable materials, and particularly relates to a preparation method of amylose-fatty acid compounds with different molecular weights.
Background
Amylose is a linear polysaccharide formed by connecting D-glucopyranose units through α -1, 4 glycosidic linkages, accounts for 20-30% of starch particles, can form a complex with various guest molecules including alcohols, polymers, iodine, fatty acids and the like through hydrophobic interactions, and is widely applied to food processing, starch-based biodegradable materials and responsive polymers.
The current common methods for preparing amylose-fatty acid complexes are mainly to grow the precipitated complexes in dimethyl sulfoxide (DMSO) -water mixtures or in acidic-alkaline solutions. DMSO or alkaline conditions cause solubilization of amylose, addition of fatty acids induces precipitation to form crystals of amylose complexes, which are separated by centrifugation and filtration to give amylose complexes. Lianxi Jun (Chinese patent CN201110120286.3) discloses a method for preparing amylose with a narrow molecular weight distribution range, which comprises the steps of carrying out enzymolysis on retrogradation resistant starch by using high-temperature amylase, dissolving the retrogradation resistant starch by using alkali liquor with the concentration of 2-4mol/L, and precipitating and separating the amylose by using n-butyl alcohol; gaoquyu et al (Chinese patent CN201710644842.4) discloses a method for preparing low amylose starch nanocrystals by enzymatic pretreatment in cooperation with an acid method.
However, there are a number of problems with the current methods. First, residual DMSO organic solvent in the purified complex interferes with experimental results, and the use of DMSO in the preparation process limits the use of the complex in food processing. Secondly, the use of alkaline and acidic solutions will lead to hydrolysis of amylose, and these processes for preparing amylose-fatty acid complexes are more complicated.
Therefore, the method for preparing amylose and amylose compound without using organic solvent or acid-base condition is simple, efficient and environment-friendly and receives more and more attention. The preparation of amylose and its compounds with controllable molecular weight is also one of the research hotspots in the fields of food processing and biodegradable materials nowadays.
Disclosure of Invention
Aiming at the technical problems, the invention provides a simple, high-efficiency and environment-friendly method for preparing amylose-fatty acid compounds with different molecular weights, which comprises the following specific preparation steps:
(1) weighing 1g of amylose, adding the amylose into deionized water, preparing an amylose suspension with the mass fraction of 5%, adding the amylose suspension into a polytetrafluoroethylene reaction kettle, adding 0.2g of fatty acid, mixing, sealing, placing the sealed reaction kettle into a ventilation oven, and vibrating and mixing for 1 hour at 85 ℃;
(2) after vibration mixing, heating the suspension in the reaction kettle to 160 ℃, stopping heating, then stirring the suspension, cooling to 100 ℃, placing the reaction kettle filled with the suspension in a ventilation oven after cooling, keeping the temperature and rotating for 24 hours at 85 ℃, and discharging after rotating to obtain an amylose-fatty acid compound;
(3) diluting the amylose-fatty acid compound with water at 85 ℃ until the mass fraction is 1%, centrifuging, removing supernatant, collecting precipitate, washing with hot water at 65-80 ℃ for 2-3 times, and freeze-drying to obtain white amylose-fatty acid compound powder.
The weight average molecular weight Mw of the amylose in the step (1) is 200000.
The fatty acid in the step (1) is any one of caprylic acid (C8), capric acid (C10), lauric acid (C12), myristic acid (C14) and palmitic acid (C16).
The centrifugal separation rotating speed in the step (3) is 2000rpm, and the centrifugal time is 5 minutes.
The amylose and the fatty acid with different carbon chain lengths are compounded, so that the molecular weight of the prepared amylose-fatty acid compound is controllable, and the weight average molecular weight Mw of the compound is 39000-190000.
The present invention prepares a series of amylose-fatty acid complexes by simply mixing various fatty acids (C8, C10, C12, C14, C16) and amylose (Mw of 200000) in a hot aqueous solution without enzymes, acid-base conditions and complicated routes through the above-mentioned steps, followed by simple separation and purification steps. The principle of the method is as follows:
first, vibratory mixing of the tetrafluoroethylene reactor at 85 ℃ was used to obtain a better mixture of fatty acids and amylose. Because the melting point range of fatty acids of different chain lengths is-7.9 ℃ to 63.1 ℃, the fatty acids will be totally dissolved by vibrating at 85 ℃;
second, the mixture was heated to 160 ℃ in a tetrafluoroethylene reactor at which temperature all amylose was dissolved, which facilitated the incorporation of fatty acid chains into the hydrophobic cavities of the amylose chains. Due to the different lengths of the fatty acid chains, amylose-fatty acid C8, amylose-fatty acid C10, amylose-fatty acid C14 and amylose-fatty acid C16 complexes are prepared respectively, and the lengths of the helical chain sections of the complexes are 2.02, 2.52, 3.53 and 4.02nm respectively. The invention selects amylose (M) with the same high molecular weightw200000) and the amylose fraction has polydispersity and includes amylose fractions of different molecular weights (lengths)The complex can be matched and complexed with fatty acids C8, C10, C14 and C16 with different lengths to form a complex, the molecular weight of the complex is 39000-190000 as the length of the fatty acid is increased from C8 to C16;
third, the amylose-fatty acid complex initially obtained was slowly cooled to 100 ℃, and then the complex was rotated at 85 ℃ for 24 hours, which allowed the formation and precipitation of a crystalline complex. Since this temperature (85 ℃) is above the onset temperature of amylose retrogradation and above the melting point of the fatty acids, both the uncomplexed amylose and the fatty acids remain in solution. Diluting the suspension of amylose-fatty acid complex with water at 85 deg.C to a mass fraction of 1%, centrifuging, discarding the supernatant containing non-complex fatty acid and amylose, collecting the precipitate, washing twice with hot water, and finally freeze-drying to obtain white powder of amylose-fatty acid complex.
The invention has the beneficial effects that:
(1) in the traditional method for preparing the amylose-fatty acid compound, the amylose with lower molecular weight is obtained by catalyzing the degradation of the amylose by enzyme or acid and alkali, and then the amylose and the fatty acid are subjected to compound precipitation through a series of preparation steps, so that the preparation route is longer and more complex, and biological agents such as protease and the like are expensive; the invention does not need acid-base conditions and complex routes, and only simply mixes various fatty acids and amylose in hot water solution to prepare a series of amylose-fatty acid compounds;
(2) the invention selects the amylose with the same high molecular weight, simply regulates and controls the fatty acid with different carbon chain lengths to obtain the amylose-fatty acid compound with different molecular weights, takes water as a solvent, avoids the residue of organic solvents and other chemical reagents, and is beneficial to the application of the amylose-fatty acid compound in the food processing industry.
Detailed Description
The invention is described in more detail below with reference to the following examples:
examples 1 to 5 were conducted by complexing caprylic acid (C8), capric acid (C10), lauric acid (C12), myristic acid (C14), palmitic acid (C16) and amylose to prepare complexes, and testing the molecular weight and distribution of the complexes.
Example 1
(1) Weighing 1g of amylose (Mw is 200000), adding into deionized water, preparing amylose suspension with mass fraction of 5%, adding into a polytetrafluoroethylene reaction kettle, adding 0.2g of octanoic acid (C8), mixing, sealing, placing the sealed reaction kettle into a ventilation oven, and mixing under vibration at 85 deg.C for 1 hr;
(2) after vibration mixing, heating the suspension in the reaction kettle to 160 ℃, stopping heating, then stirring the suspension, cooling to 100 ℃, placing the reaction kettle filled with the suspension in a ventilation oven after cooling, and keeping the temperature and rotating for 24 hours at 85 ℃ to obtain an amylose-fatty acid compound;
(3) diluting the amylose-fatty acid compound with water at 85 ℃ to 1 mass percent, centrifuging at 2000rpm for 5 minutes, discarding the supernatant, collecting the precipitate, washing with 65 ℃ hot water for 2 times, and freeze-drying to obtain white amylose-fatty acid compound powder.
Example 2
(1) Weighing 1g of amylose (Mw is 200000), adding into deionized water, preparing amylose suspension with mass fraction of 5%, adding into a polytetrafluoroethylene reaction kettle, adding 0.2g of capric acid (C10), mixing, sealing, placing the sealed reaction kettle into a ventilated oven, and mixing under vibration at 85 deg.C for 1 hr;
(2) after vibration mixing, heating the suspension in the reaction kettle to 160 ℃, stopping heating, then stirring the suspension, cooling to 100 ℃, placing the reaction kettle filled with the suspension in a ventilation oven after cooling, and keeping the temperature and rotating for 24 hours at 85 ℃ to obtain an amylose-fatty acid compound;
(3) diluting the amylose-fatty acid compound with water at 85 ℃ to 1 mass percent, centrifuging at 2000rpm for 5 minutes, discarding the supernatant, collecting the precipitate, washing with hot water at 70 ℃ for 2 times, and freeze-drying to obtain white amylose-fatty acid compound powder.
Example 3
(1) Weighing 1g of amylose (Mw is 200000), adding into deionized water, preparing amylose suspension with mass fraction of 5%, adding into a polytetrafluoroethylene reaction kettle, adding 0.2g of lauric acid (C12), mixing, sealing, placing the sealed reaction kettle into a ventilated oven, and mixing under vibration at 85 deg.C for 1 hr;
(2) after vibration mixing, heating the suspension in the reaction kettle to 160 ℃, stopping heating, then stirring the suspension, cooling to 100 ℃, placing the reaction kettle filled with the suspension in a ventilation oven after cooling, and keeping the temperature and rotating for 24 hours at 85 ℃ to obtain an amylose-fatty acid compound;
(3) diluting the amylose-fatty acid compound with water at 85 ℃ to 1 mass percent, centrifuging at 2000rpm for 5 minutes, discarding the supernatant, collecting the precipitate, washing with hot water at 70 ℃ for 2 times, and freeze-drying to obtain white amylose-fatty acid compound powder.
Example 4
(1) Weighing 1g of amylose (Mw is 200000), adding into deionized water, preparing amylose suspension with mass fraction of 5%, adding into a polytetrafluoroethylene reaction kettle, adding 0.2g of myristic acid (C14), mixing, sealing, placing the sealed reaction kettle into a ventilated oven, and mixing under vibration at 85 deg.C for 1 hr;
(2) after vibration mixing, heating the suspension in the reaction kettle to 160 ℃, stopping heating, then stirring the suspension, cooling to 100 ℃, placing the reaction kettle filled with the suspension in a ventilation oven after cooling, and keeping the temperature and rotating for 24 hours at 85 ℃ to obtain an amylose-fatty acid compound;
(3) diluting the amylose-fatty acid compound with water at 85 ℃ to 1 mass percent, centrifuging at 2000rpm for 5 minutes, discarding the supernatant, collecting the precipitate, washing with hot water at 75 ℃ for 2 times, and freeze-drying to obtain white amylose-fatty acid compound powder.
Example 5
(1) Weighing 1g of amylose (Mw is 200000), adding into deionized water, preparing amylose suspension with mass fraction of 5%, adding into a polytetrafluoroethylene reaction kettle, adding 0.2g of palmitic acid (C16), mixing, sealing, placing the sealed reaction kettle into a ventilated oven, and mixing under vibration at 85 deg.C for 1 hr;
(2) after vibration mixing, heating the suspension in the reaction kettle to 160 ℃, stopping heating, then stirring the suspension, cooling to 100 ℃, placing the reaction kettle filled with the suspension in a ventilation oven after cooling, and keeping the temperature and rotating for 24 hours at 85 ℃ to obtain an amylose-fatty acid compound;
(3) diluting the amylose-fatty acid compound with water at 85 ℃ to 1 mass percent, centrifuging at 2000rpm for 5 minutes, discarding the supernatant, collecting the precipitate, washing with hot water at 80 ℃ for 3 times, and freeze-drying to obtain white amylose-fatty acid compound powder.
The results of the amylose-fatty acid tests prepared in examples 1, 2 and 4 are shown in table 1:
TABLE 1 molecular weight test results for amylose-fatty acids
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101914163A (en) * | 2010-08-26 | 2010-12-15 | 华南理工大学 | A kind of slowly digested starch and preparation method thereof |
| CN103288972A (en) * | 2013-06-28 | 2013-09-11 | 山东农业大学 | Method for producing stearic acid starch ester through homogeneous dry process |
| CN104961837A (en) * | 2015-06-30 | 2015-10-07 | 华南理工大学 | Preparation method of starch and fatty acid compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101914163A (en) * | 2010-08-26 | 2010-12-15 | 华南理工大学 | A kind of slowly digested starch and preparation method thereof |
| CN103288972A (en) * | 2013-06-28 | 2013-09-11 | 山东农业大学 | Method for producing stearic acid starch ester through homogeneous dry process |
| CN104961837A (en) * | 2015-06-30 | 2015-10-07 | 华南理工大学 | Preparation method of starch and fatty acid compound |
Non-Patent Citations (1)
| Title |
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| Effect of fatty acids on the rheological behaviour of amylomaize;Stylianos N. Raphaelides et al.;《Food Research International》;20071018;第44卷(第1期);第75-78页 * |
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